Assistant Payroll Manager

Assistant Payroll Manager – Remote (Must be Chicago Area)

Location: Remote – Must reside within commutable distance to Chicago area.

Pay Rate: $30–$33 per hour

Job Type: Full-Time Contract | Potential for Long-Term Extension or Permanent Conversion

Initial Contract: 3 Months

Schedule: Monday–Friday | 40 Hours per Week

About the Opportunity

The Midtown Group is seeking an experienced Assistant Payroll Manager to support payroll operations for a well-established national organization.

This is a primarily remote opportunity , but candidates must reside within commuting distance of Addison, IL 60101 , as occasional onsite attendance may be required for meetings, training, or business needs.

The position begins as a three-month contract, with the potential to extend into a longer-term assignment or convert to a permanent position based on business needs and performance.

We are looking for a hands-on payroll professional who understands the full payroll lifecycle, enjoys working with cross-functional teams, and can support complex payroll operations. This individual will work closely with the Payroll Manager, with the opportunity to take on additional responsibilities over time.

Key Responsibilities

• Support accurate and timely biweekly payroll processing for 1,000+ employees across multiple states.
• Review employee payroll information, salary adjustments, benefits deductions, garnishments, and other payroll-related transactions.
• Work with Workday, ADP, Fidelity, and other payroll and benefits vendors to support payroll operations and ensure data accuracy.
• Collaborate with Human Resources, Accounting, employees, and external vendors to resolve payroll discrepancies.
• Ensure employee deductions and related vendor payments are accurate and processed on time.
• Review and support payroll-related general ledger postings, journal entries, and account reconciliations.
• Assist with employee expense reimbursements and payroll-related inquiries.
• Prepare payroll reports and provide information for management review.
• Support internal audits, compliance activities, and payroll process improvements.
• Help troubleshoot payroll system issues and coordinate resolutions with internal teams and external providers.
• Provide operational support and oversight as needed, with the potential to assume greater payroll management responsibilities.

Qualifications

• 3–5+ years of hands-on payroll processing experience , preferably supporting mid-sized to large organizations.
• Strong understanding of full-cycle payroll processing, including biweekly payroll cycles.
• Workday experience strongly preferred.
• Experience with ADP and/or Fidelity is highly desirable.
• Knowledge of payroll deductions, benefits administration, garnishments, and multi-state payroll requirements.
• Understanding of general ledger accounting, payroll journal entries, and reconciliations.
• Experience researching and resolving payroll discrepancies.
• Strong Microsoft Excel skills and comfort working with payroll systems and reporting tools.
• Excellent organizational, analytical, and communication skills.
• Ability to work independently in a remote environment while collaborating with cross-functional teams.
• Previous payroll leadership, oversight, or process improvement experience is a plus.
• Familiarity with emerging technologies and AI productivity tools, such as Microsoft Copilot or Claude, is a plus.

Industry experience is flexible! Candidates with strong payroll processing backgrounds across any industry are encouraged to apply.

Work Arrangement

This position is remote for the majority of the initial contract assignment , with occasional onsite attendance required based on business needs.

Applicants must live within reasonable commuting distance of Addison, IL 60101. Candidates must be comfortable reporting onsite when requested.

If the position converts to permanent employment, the hybrid schedule and onsite expectations may change.

Why Consider This Opportunity?

• Competitive hourly pay of $30–$33/hour .
• Primarily remote work arrangement.
• Opportunity to support a large, multi-state payroll operation.
• Exposure to Workday, ADP, Fidelity, and additional enterprise payroll systems.
• Collaborative environment with opportunities to contribute to payroll process improvements.
• **Potential for long-term contract extension or permanent employme…